


Dress to Impress

by KillerOfHope



Category: Supernatural
Genre: Alternate Universe - Always a Different Sex, Case Fic, Dom/sub Play, F/M, Female Dean Winchester
Language: English
Status: Completed
Published: 2020-07-24
Updated: 2020-07-24
Packaged: 2021-03-04 21:08:03
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,198
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25482916
Author URL: https://archiveofourown.org/users/KillerOfHope/pseuds/KillerOfHope
Summary: Prompt:Deanna and Sam are undercover as a married couple in a gated community where several strange murders have taken place while undercover, the two have a little roleplay in the bedroom as 'husband and wife' with Sam as the dom Hubby and Deanna being the ever submissive wife, taking every order he gives, referring to Sam at some point as 'sir'.
Relationships: Dean Winchester/Sam Winchester
Kudos: 91





	Dress to Impress

Deanna has to admit that something about this is incredibly exciting. When Bobby called, she expected the worst. A closed of community, which were incredibly suspicious of strangers yet couldn't solve a little murder problem on their own. In the end, Deanna only agreed because lives were at stake and Bobby truly had no one else to ask. Well, he's one of the few people who actually know how close the Winchester Boys truly are.

Boys, ha. Just another of John Winchester's well-kept secrets. Though for once Deanna doesn't mind and even Sam admits it has its uses. Running around as a man is a lot safer in their world. Since she prefers jeans over skirts, hates makeup and knows how to handle the Impala better than Sammy does, no one in their immediate family ever objected. Well, Jo did. But Jo could go fuck herself for all Deanna cared.

She isn't picky about pronouns. No, she doesn't want to change her gender, thank you very much.

There's no one with the right to care since Sam is the only one allowed to touch her anyway. Deanna is picky about that.

So, running around as a woman is actually new for her.

Her heart is beating against her ribcage as they enter the bar. Well, it advertises as a restaurant, but since it's the only one in the entire village, it functions as bar, dinner and town hall all rolled into one. Nothing new, except Deanna is wearing a short skirt, a push-up bra and a shirt that reveals her breasts in a way she never dared to show before. Not with John Winchester's voice in her head to _be careful, the best defence you have is that people don't know what you're hiding_ _under your sweater_.

"You're doing well," Sam tells her and sends her the smile of an adoring husband. Someone, who he's incredibly proud of his wife and Deanna's legs tingle at the sight of it. "Just relax and remember we're here to do our job."

"Easy for you to say," Deanna murmurs under her breath.

She has done this kind of work before, though it's usually Sam who gets women to open up. It's his easy smile, his caring attitude while Deanna's just screams 'fuck off', his extended knowledge about a healthy diet ... well, and his looks. Deanna can't deny that. There's a reason, why she never looked at another man once Sammy got legal and John Winchester disappeared into the woods somewhere.

Sam's large hand settles on her back and they both smile as they're greeted by the town sheriff. Deanna ignores how the possessive gesture makes her wet already, right here in public, because these kinds of touches are usually reserved for the privacy of their motel room.

"You must be the nice and lovely couple, we've heard so much about," the barwoman exclaims, sending the Winchester's a nice and welcoming smile.

  
  


* * *

  
  


"These people have strange ideas," Deanna complains when they're finally allowed to retire for the night. "I think, they're still trapped in the fucking Middle Ages."

The evening was hell on both of them and after a while, Deanna got, why the hunter before them had so much trouble. It was less, because of the difficulty of the case. It was rather that the town people didn't talk to strangers. Or anyone in general, who doesn't fit into their world view. Which included wives obeying their husbands, not talking back, having no jobs and doing household chores.

"If it weren't for the kids, I'd opt for leaving town," Sam murmurs under his breath, looking just as furious as Deanna felt. "Too much trouble for a simple salt and burn."

"I hear you, Sammy," Deanna whispers, as they enter the bedroom.

Since it's locked directly above the dinner, the town is incredibly small and doesn't have its own motel, they need to be careful. Reports from the last hunter said that the people liked to spy on you. Which had been partly the reason, why he had to leave in the first place. Leaving an angry ghost, three more murders and frightened townspeople in his wake.

"Ready for step two?" Sam wants to know, pulling Deanna close.

"Always," his sister says and grins. "Ever since I had to dress up in this tight little skirt."

Sam chuckles. Of course, Deanna doesn't mind keeping up the little role-play they have going here. According to the last hunter, they would need to please the major first or else they would never get the information which damned grave they had to dig up. Same said major, who's the father of the barwoman and who is going to get a report next morning if the nice young couple is behaving properly. Since they came with the story of maybe buying a house up here, raising their future children in a nice and safe environment, it's crucial to earn their trust.

And truly, Deanna has done worse for a case than play the submissive obedient wife.

  
  


* * *

  
  


A quick survey through the room confirms that they're being watched. Deanna spots a few holes in the wall while she makes a show of unpacking the harmless contents of their duffles and Sam sends her a warning look when he returns from the bathroom. Whatever this town's deal is, they need to play along.

"Dear?" Deanna asks, in the same manner, she has seen women do in movies. "Do you believe we'd be able to settle down here?"

It's an innocent question of a concerned wife, but for Deanna, it feels like she stepped into a bad porn movie. She knows what the woman behind the thin wall expects. For Deanna to kneel before her husband, obey his orders and be glad to get fucked by him. God, it's not as if they didn't play rough before, Deanna thinks as she watches Sam put away his shoes. But this kind of roleplay is different from all the times when Sammy lifts her up and fucks her against a wall after a case. Or bends her over the Impala and teases her endlessly until she's crying tears.

He must've read something in her expression, because he says, "Don't worry, I'm going to take care of you."

A perfect answer for the fearful wife who doesn't want to raise children in a town, where people are getting murdered. Also perfectly whispered into her ear as Sam pulls her closer and grabs her ass as if it belongs to him.

Her breath hitches at that thought. It feels good, the way Sam takes charge, kisses her like he has kissed her a thousand times. It's familiar and yet ... usually he goes along with what Deanna wants. She's the one, who plays the sullen mulish sibling, the one who straddles his lap during research, the one who slips a hand into his boxers when she wants something.

Today it's Sam, who keeps his expression smooth while his hand wanders under her skirt. His long, thick fingers rub over her panties and he smirks as he finds them soaked and wet.

"You're a good wife, being ready for me," Sam says and encourages her quiet moans to become louder as he rubs her clit through the denim. "It's a special occasion, my love, searching for a house to settle down and I'm pleased to see you agree with me."

"Yes, dear," Deanna gasps, as Sam plays with the panties she bought. They were wet before because Deanna couldn't quite hide her nervousness. But now they're soaked, sticking to her skin and make squishy noises as Sam pushes them into her wet fold.

Usually, Deena would demand to be fucked right now. With at least one person in the other bedroom, she has to bite down on her lips in order to hold herself back. God, she's not going to last long if Sam keeps teasing her like this.

Sam pushes up her top, frees her breasts and pinches her left nipple, hard. The bra is quality work for once, lingerie Deanna refuses to buy because they are useless on hunts, but today she can see the appeal.

"Look how eager you're," Sam tells her, in a soothing yet commanding voice as if he knows her body better than her. "See how fast your nipples are getting hard? I wouldn't be able to do that if you didn't feel safe here."

For the listeners, it must sound as if Sam means this town.

"You're right, darling."

Deanna is surprised how out of breath she is. She isn't even doing anything, keeping her hands at her sides, because she wants to see what Sam is going to do. Is even a little curious herself how far she can take this little game and so far she's amazed by her own eagerness to keep still, just in order to please someone. She leaves it to Sam, what comes next and even the simple gesture of guiding her towards the bed is different now. Instead of dragging him by his wrist, shoving her brother down and riding him into oblivion, Deanna allows Sam to fondle her breasts, gives him free access to her body all while slowly walking backwards.

"I want you to be good for me," Sam tells her and removes her clothing until she's only dressed in wet panties. His fingers are rubbing her clit again, teasing her until she mewls. "Remember that I know what's best for you."

"Yes, sir," Deanna breathes, already on the brink of her arousal, because she isn't allowed to touch Sam. She has to ask first and self-restraint has never been her strong point. "May I touch you?"

A little noise behind the wall tells Deanna that they are being watched and hopes that it's enough to blow Sam. That's what a good wife does, isn't it? But Sam has different ideas.

"No, you may not," he says and goes on his knees, kneeling before her. "You can hold onto the table, for all I care. But you're not allowed to touch me or yourself."

With that, Sam's head vanishes between her legs and Deanna moans as her brother starts eating her out. It's thoroughly embarrassing how quickly she's arching into his mouth, riding his tongue and pleads whenever he pulls back. Even the kisses on her inner thigh are just another form of torture.

"Oh...oh, dear," she cries out as a single finger slips into her wet pussy.

It goes in so easily, but Sam still insists on taking his time that Deanna suspects he intends to drive her mad.

"Baby, you need to stay quiet," Sam croons and slowly pulls her panties down. "We're guests in this house and it'd be impolite to wake Mrs Teal."

"Of course... - hhmpf"

Deanna chokes a little as Sam puts the panties in her mouth. Her wet soaked panties, which she has been wearing all day and are now functioning as the perfect gag. It's dirty and indecent, but she doesn't spit them out. Instead, Deanna allows Sam to manhandle her. She's so close to coming, but with trembling legs, she holds it back as Sam bends her over until Deanna is holding onto solid wood, her ass and her pussy exposed.

"Do you want me to touch you here?" Sam asks innocently as she unclasps her bra and fondles her bouncing breasts. Deanna moans around the panties because her brother beautiful dick is still trapped in his pants, though rubbing against her backside. As promised, what could happen? So it's not exactly a surprise when Sam's hands wander up and down her sides until his fingers find the cleft of her ass. "Or would you rather I touch you there?"

Sam enjoys the way his sister twitches and slowly pulls her cheeks apart. Deanna is so wet and painfully aroused that he could fuck her ass with ease. Testing her reaction, Sam presses a knuckle inside and gets a dirty moan.

"Are you scared?" Sam asks though he feels how Deanna clenches around him. Rocking back on them and twisting her neck, because she can't use her mouth to beg. That she shakes her head is reassuring because it's difficult to say if they're still being watched. Since Sam reaches a point, where he stops caring about possible voyeurs, he says, "Do want something there? Get your ass filled? I bed no one in this little town could ever guess how dirty you're. What will you do to keep your husband happy."

To tease her further Sam pushes the finger deeper, slowly fucking her at an incredibly slow pace she normally wouldn't allow. Today she has to obey. And it doesn't look like as if she's not enjoying it. In fact, as Sam coats his fingers in the juices running down her legs and pushes two of them inside the tight hole of her ass, Deanna nearly screams with pleasure. Only the makeshift gag keeps her from waking up the entire house as she clenches around his hand.

"Just imagine it how it would feel like if you are riding my cock," Sam murmurs and drags her towards the bed.

  
  


**Author's Note:**

> Old Fic which I never publish, because I hoped I could find a better ending. In the end, I decided against it, because this is not the version of 'female Dean' I want to write, but it was while it lasted. If I return to a female Dean, I'd go differently at exploring how she would see herself and what kind of consequences being 'John Winchester's Daughter' would have.


End file.
